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Holiday Rentals in Oregon

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Holiday Rentals in Oregon

Spacious & Modern Home w/ Deck in Oregon!

Spacious & Modern Home w/ Deck in Oregon!

Spacious 5-bedroom house sleeps 14 with pool, hot tub, sauna and more!

10.0 out of 10, Exceptional, (2)
"Perfect location for a family get together. Away from the hustle bustle, but close enough to restaurants and stores. House is clean, spacious and the pool is well maintained."
Spacious 5-bedroom house sleeps 14 with pool, hot tub, sauna and more!

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (66)
"Nice place very cozy"
The Dylin

Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

3.2 out of 10, (10)
"Couldnt even sleep there the place smelled like straight cat pee and had real feces present horrible cant believe they allow this place to stay on VRBO"
The price is €215
includes taxes & fees
23 Jun - 24 Jun
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (19)
"What a great spot right on the lake and near a lot of great restaurants and places. "
The price is €351
includes taxes & fees
24 Jun - 25 Jun
One Bedroom King with Den with views of Lake Monona in the heart of downtown.

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (28)
"Supper clean, comfortable beds and great location. Will definitely stay here again. "
The price is €386
includes taxes & fees
30 Jun - 1 Jul
Two bedroom suite with city views in the heart of downtown Madison

Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!

9.8 out of 10, Exceptional, (154)
"We have been coming here for several years and love it. Super quiet neighborhood, home is clean and well maintained, Tammy is a great host and quick to answer messages. We will be back again next year!"
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!

Charming 2-bedroom cottage on Lake Koshkonong in Fort Atkinson, Wi.

10.0 out of 10, Exceptional, (1)
"Very cozy, wonderful amenities, greeted with a fresh bouquet of flowers, highly recommend!"
Charming 2-bedroom cottage on Lake Koshkonong in Fort Atkinson, Wi.

Kosh Cottage - Beach Vibes & Gorgeous Sunrises!

2.0 star property
Kosh Cottage - Beach Vibes & Gorgeous Sunrises!

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (57)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

Lakefront Access Cottage on Lake Koshkonong

10.0 out of 10, Exceptional, (6)
"Great little place with convenient access to Fort. It was nice to be a short walk to the lake. Fantastic hosts with very quick communication"
Lakefront Access Cottage on Lake Koshkonong

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (138)
"It was a very nice place. Clean, spacious, unique and quiet. Very good communication, quick response from host whenever I had questions. We definitely recommend this place and love to stay again if we have a chance. "
ONE OF A KIND vacation rental with a view

Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL

10.0 out of 10, Exceptional, (28)
"Had a great one month stay. Clean lake great beach nearby lots of toys including pontoon boat kayaks and sailboat cottage was very spaceous and clean. Highly recommend "
Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

10.0 out of 10, Exceptional, (142)
"We enjoyed our stay, peaceful, clean and everything we needed. "
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Charming 4-bedroom Lake house on Lake Ripley in Cambridge

10.0 out of 10, Exceptional, (8)
"Really enjoyed the space "
Charming 4-bedroom Lake house on Lake Ripley in Cambridge

Right on the Water! Private Pier, Excellent Sunsets & Swimming

9.6 out of 10, Exceptional, (96)
"I give this rental a five stars overall. The property contact was very responsive. The location so close to the lake is just perfect. Great for a girls weekend away. Only constructive feedback. Is there a couple of things that should be repaired on the property, such as a cracked sink, But nothing that overall affected the functionality of the rental for us. Neighbors were very quiet and we would definitely stay here again."
Right on the Water! Private Pier, Excellent Sunsets & Swimming

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (19)
"Everything we needed easy commute to city of wisconson, clean, great communication with the host and the host left a welcome basket for us that was focused towards the reason we were in town, world championship strongman competition. "
Paoli Den - Newly Remodeled!

On the Yahara River, access to Madison Lakes

10.0 out of 10, Exceptional, (35)
"A must stay if you’re in the Madison area. "
On the Yahara River, access to Madison Lakes

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (32)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Are there holiday rentals in Oregon?

Yes, there are holiday rentals close to the most popular sights in Oregon, or you can select a more secluded option if you're looking for a relaxing stay. Oregon is known for its golf courses.

What are some of the best holiday rentals that Oregon has to offer?

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect: This holiday home rental outside of Oregon is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Oregon?

Choose from 3 Expedia holiday rentals in Oregon for a memorable holiday.

What can I see and do in Oregon?

Explore the area and family-friendly sights such as Verona Ice Arena, or get out into nature at a spot like Lake Waubesa. In the wider area, you’ll find Legend at Bergamont and Wisconsin Brewing Company.

What are holiday rentals like in Oregon?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oregon. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.